IVAS 2022 banner
IVES 9 IVES Conference Series 9 IVAS 9 IVAS 2022 9 Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Abstract

(+)-Catechin—laccase oxidation dimeric standards were hemi-synthesized using laccase from Trametes versicolor in a water-ethanol solution at pH 3.6. Eight fractions corresponding to eight potential oxidation dimeric products were detected. The fractions profiles were compared with profiles obtained with two other oxidoreductases: polyphenoloxidase extracted from grapes and laccase from Botrytis cinerea. The profiles were very similar, although some minor differences suggested possible dissimilarities in the reactivity of these enzymes. Five fractions were then isolated and analyzed by 1D and 2D NMR spectroscopy. The addition of traces of cadmium nitrate in the samples solubilized in acetone-d6 led to fully resolved NMR signals of phenolic protons, allowing the unambiguous structural determination of six reaction products, one of the fractions containing two enantiomers. These products were then analyzed in grape seed extracts and red wines (UHPLC-Q-Orbitrap MS). The different dimers had different fragmentation patterns according to their interflavan linkage position. Oxidation dimeric compounds had a specific fragment ion at m/z 393, missing for B-Type dimers fragmentations. A fragment ion at m/z 291 occurred and was specific for oxidation dimeric compounds with a C-O-C linkage. Higher level oxidation products had abundant specific fragments: m/z 425, 397 and 245. These fragmentations were useful to identify them in complex samples such as grape seed extracts and wines. Three grape varieties and three ripening stages were selected and the corresponding seed extracts were obtained. The analyses revealed an increasing trend for the oxidation markers during grape ripening. The analysis of Syrah wines (2018, 2014, 2010) showed a decreasing trend of these molecules during wine ageing which might be due to further oxidation.

DOI:

Publication date: June 23, 2022

Issue: IVAS 2022

Type: Article

Authors

Saucier Cedric1, Deshaies Stacy1, Le Guernevé Christine1,2, Sommerer Nicolas1,2, Garcia Lucas Suc François1, Mouls Laetitia1

1SPO, Université de Montpellier, INRAE, Institut Agro, UMR SPO, Faculté de Pharmacie, 15 avenue Charles Flahault, 34000 Montpellier, France
2INRAE, PROBE Research Infrastructure, PFP Polyphenol Facility, 34060 Montpellier, France

Contact the author

Keywords

wine, grape, polyphenol,oxidation, catechin

Tags

IVAS 2022 | IVES Conference Series

Citation

Related articles…

Amino nitrogen content in grapes: the impact of crop limitation

As an essential element for grapevine development and yield, nitrogen is also involved in the winemaking process and largely affects wine composition. Grape must amino nitrogen deficiency affects the alcoholic fermentation kinetics and alters the development of wine aroma precursors. It is therefore essential to control and optimize nitrogen use efficiency by the plant to guarantee suitable grape nitrogen composition at harvest. Understanding the impact of environmental conditions and cultural practices on the plant nitrogen metabolism would allow us to better orientate our technical choices with the objective of quality and sustainability (less inputs, higher efficiency). This trial focuses on the impact of crop limitation – that is a common practice in European viticulture – on nitrogen distribution in the plant and particularly on grape nitrogen composition. A wide gradient of crop load was set up in a homogeneous plot of Chasselas (Vitis vinifera) in the experimental vineyard of Agroscope, Switzerland. Dry weight and nitrogen dynamics were monitored in the roots, trunk, canopy and grapes, during two consecutive years, using a 15N-labeling method. Grape amino nitrogen content was assessed in both years, at veraison and at harvest. The close relationship between fruits and roots in the maintenance of plant nitrogen balance was highlighted. Interestingly, grape nitrogen concentration remained unchanged regardless of crop load to the detriment of the growth and nitrogen content of the roots. Meanwhile, the size and the nitrogen concentration of the canopy were not affected. Leaf gas exchange rates were reduced in response to lower yield conditions, reducing carbon and nitrogen assimilation and increasing intrinsic water use efficiency. The must amino nitrogen profiles could be discriminated as a function of crop load. These findings demonstrate the impact of plant balance on grape nitrogen composition and contribute to the improvement of predictive models and sustainable cultural practices in perennial crops.

Teasing apart terroir: the influence of management style on native yeast communities within Oregon wineries and vineyards

Newer sequencing technologies have allowed for the addition of microbes to the story of terroir. The same environmental factors that influence the phenotypic expression of a crop also shape the composition of the microbial communities found on that crop. For fermented goods, such as wine, that microbial community ultimately influences the organoleptic properties of the final product that is delivered to customers. Recent studies have begun to study the biogeography of wine-associated microbes within different growing regions, finding that communities are distinct across landscapes. Despite this new knowledge, there are still many questions about what factors drive these differences. Our goal was to quantify differences in yeast communities due to management style between seven pairs of conventional and biodynamic vineyards (14 in total) throughout Oregon, USA. We wanted to answer the following questions: 1) are yeast communities distinct between biodynamic vineyards and conventional vineyards? 2) are these differences consistent across a large geographic region? 3) can differences in yeast communities be tied to differences in metabolite profiles of the bottled wine? To collect our data we took soil, bark, leaf, and grape samples from within each vineyard from five different vines of pinot noir. We also collected must and a 10º brix sample from each winery. Using these samples, we performed 18S amplicon sequencing to identify the yeast present. We then used metabolomics to characterize the organoleptic compounds present in the bottled wine from the blocks the year that we sampled. We are actively in the process of analysing our data from this study.

Protected Designation of Origin (D.P.O.) Valdepeñas: classification and map of soils

The objective of the work described here is the elaboration of a map of the different types of vineyard soils that to guide the famers in the choice of the most productive vine rootstocks and varieties. 90 vineyard soils profiles were analysed in the entire territory of the Origen Denominations of Valdepeñas. The sampling was carried out in 2018 (June to October) by making a sampling grid, followed by photointerpretation and control in the field. The studied soils can be grouped into 9 different soil types (according to FAO 2006 classification): Leptosols, Regosols, Fluvisols, Gleysols, Cambisols, Calcisols, Luvisols and Anthrosols. A map showing the soil distribution with different type of soils has been made with the ArcGIS program. Regarding to the choice of rootstock, Calcisoles are soils with a high active limestone content, so the rootstocks used in these soils must be resistant to this parameter; Luvisols are deep soils with high clay content, so they will support vigorous rootstocks. Because the cartographic units are composed of two or more subgroups, with are associated in variable proportions, 9 different soil associations have been established; Unit 1: Leptosols, Cambisols and Luvisols (80%, 15% and 5% respectively); Unit 2: Cambisols with Regosols and Luvisols (40%, 30% and 30% respectively); Unit 3: Cambisols and Gleysols with Regosols (40%, 40% and 20% respectively); Unit 4: Regosols with Cambisols, Leptosols and Calcisols (40%, 30%, 15% and 15% respectively); Unit 5: Cambisols, Leptosols, Calcisols and Regosols (25% each of them); Unit 6: Luvisols with Cambisol and Calcisols (80%, 10% and 10% respectively); Unit 7: Luvisols and Calcisols with Cambisols (40%, 40% and 20% respectively); Unit 8: Calcisols with, Cambisols and Luvisols (80%, 10% and 10% respectively); Unit 9: Anthrosols. These study allow to elaborate the first map of vineyard soils of this Protected Designation of Origin in Castilla-La Mancha.

Postveraison shoot trimming in Tannat and Merlot: preliminary results on yield components, plant balance and berry composition

There is currently a trend towards the production of wines with low alcohol content. To achieve this, grapes with low sugar content must be used. There are techniques at the vineyard level that can delay ripening and avoid excessive sugar accumulation without, a priori, affecting the final polyphenol content. Postveraison shoot trimming (PVST) is experimentally evaluated for these purposes, but its impact under Uruguayan climatic conditions with high interannual variability is not known. The aim of this work is to assess the PVST in Tannat and Merlot cultivars and their impact on yield components, plant balance and berry primary composition. In this study, two commercial vineyards of 10 years old Tannat and Merlot (grafted on SO4) at Canelones Department were selected. During the 2020-201 growing season, grapevines were submitted to PVST when grapes reached 15º Brix. In a randomized block, trimmed (T) and control (C) plants were evaluated with three repetitions each cultivar. Evaluation of the evolution of primary berry composition during ripening, measurement of yield components and plant balance were performed. For both cultivars, PVST did not affect yield components. Merlot reached 5.4 kg per plant and Tannat 7.1 kg, with not statistical significance between treatments. However, statistical differences were observed in terms of plant balance. In Merlot Ravaz Index reached a difference of 5.3 (12.0 in T and 6.7 in C) meanwhile Tannat reached 3.5 of statistical difference (13.7 in T and 10.2 in C). The tendency to imbalance for the treated plants had an impact on the final grape composition. Merlot grapes showed statistical difference in final total acidity (0.3 g of difference between treatments) while treatments impact final sugar content on Tannat grapes (10.0 g of difference between treatments). Further studies are needed to assess the impact of different canopy management techniques in our conditions.

Grapevine yield-gap: identification of environmental limitations by soil and climate zoning in Languedoc-Roussillon region (south of France)

Grapevine yield has been historically overlooked, assuming a strong trade-off between grape yield and wine quality. At present, menaced by climate change, many vineyards in Southern France are far from the quality label threshold, becoming grapevine yield-gaps a major subject of concern. Although yield-gaps are well studied in arable crops, we know very little about grapevine yield-gaps. In the present study, we analysed the environmental component of grapevine yield-gaps linked to climate and soil resources in the Languedoc Roussillon. We used SAFRAN data and IGP Pays d’Oc wine yields from 2010 to 2018. We selected climate and soil indicators proving to have a significant effect on average wine yield-gaps at the municipality scale. The most significant factors of grapevine yield were the Soil Available Water Capacity; followed by the Huglin Index and the Climatic Dryness Index. The Days of Frost; the Soil pH; and the Very Hot Days were also significant. Then, we clustered geographical zones presenting similar indicators, facilitating the identification of resources yield-gaps. We discussed the number of zones with the experts of IGP Pays d’Oc label, obtaining 7 zones with similar limitations for grapevine yield. Finally, we analysed the main resources causing yield-gaps and the grapevine varieties planted on each zone. Mapping grapevine resource yield-gaps are the first stage for understanding grapevine yield-gaps at the regional scale.